Greenwich Estate Once Owned by Leona Helmsley Seeks $49.895 Million

On roughly 40 acres overlooking Long Island Sound, the property includes an Elizabethan-style brick house measuring about 17,000 square feet

Leona Helmsley’s onetime estate in Greenwich, Conn., is relisting for $49.895 million, a 23% reduction from its asking price two years ago.

The Elizabethan-style brick house was listed for $65 million with David Ogilvy & Associates in 2014, though the price had been reduced to $58 million by the time it was taken off the market last winter, said co-listing agent Bill Andruss of Sotheby’s International Realty.

In Greenwich, “we’re seeing a bit of a sluggish market” due to it being an election year and a lot of inventory on the market, said Mr. Andruss, who will be listing the property with colleagues Leslie McElwreath and Joseph Barbieri. He added that sales over $20 million in Greenwich are somewhat rare. He said his aim in repricing the property was “to reach a level that I think will create interest.”

Spanning roughly 40 acres overlooking Long Island Sound, the estate includes a nine-bedroom house measuring about 17,000 square feet with 11 wood-burning fireplaces, Mr. Andruss said. The first floor contains several grand entertaining rooms, including a 42-foot-long living room with a plaster tracery ceiling, a dining room with travertine floors and an oak-paneled library.

Cyd L. Smith, attorney for the sellers, said they bought the gated property from the Helmsley estate in 2010 for $35 million and drew up plans for an extensive renovation. They then “had a change of heart in terms of living at the property,” she said, and put it back on the market less than a year later for nearly $43 million. It has been on and off the market ever since.

Once among New York City’s biggest landlords, Ms. Helmsley and her husband, Harry, bought the property for $11 million in 1983. Ms. Helmsley was convicted of tax evasion and sentenced to 16 years in prison, though she served less than two. She died in 2007 at age 87.